Acetic Acid → HCID 20478387, compound

Participants

Reaction Steps

A solution of the product of step (a) (4.0 g) and diethyloxalate (13.0 g) in dry dimethylformamide (275 ml) was slowly added to a stirred suspension of ether washed sodium hydride (50% dispersion in oil, 2.1 g) in dry dimethylformamide (225 ml) under an atmosphere of nitrogen. The resulting suspension was stirred for 1 week then poured into water (1000 ml). The solution formed was acidified with glacial acetic acid, made saline with brine, extracted with ethyl acetate (2×500 ml), washed with water, dried and evaporated to give a brown oil. This oil was dissolved in dry dioxan and dry hydrogen chloride gas was bubbled through it for 15 minutes. The solution was then poured into water, extracted with ethyl acetate (2×300 ml), dried and evaporated to give a yellow brown solid which gave the sub-title compound (1.5 g) after chromatography (SiO2 /3:2 40°-60° petroleum ether/ether) as yellow crystals.

Provenance & Evidence